Triacetoxyperiodinane → (1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanone

HRID 1515771Notes

Reaction equation

HRID 1515771 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:21]([C:23]2[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=2)[OH:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[C:25]([C:31]([F:32])([F:33])[F:34])[CH:24]=2)=[O:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67229413(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanol

Product 1

HCID 67228718(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 250 mL round bottomed flask charged with ((1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanol (5.08 g, 10 mmol) and dichloromethane (50 mL) was added Dess-Martin periodinane (10.65 g, 25 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 2 h before quenching with saturated aqueous sodium bicarbonate solution (100 mL). The mixture was extracted with ethyl acetate (250 mL), washed with saturated aqueous sodium bicarbonate solution (3×50 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give (1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanone as a light yellow solid (4.3 g, 85%) which was used for the next step without further purification: LC/MS m/e calcd for C23H18F3N2O4S2 [M+H]+ 507.06, observed 507.0.

Workup

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (100 mL)
  2. extractionThe mixture was extracted with ethyl acetate (250 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (3×50 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39c46152412f4713a99eadaf7ab78a87
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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